oh…how about Leonard Cohen?
Etta James
Billie Holiday
Sam Cooke
Lou Reed
George Clinton
Anne Clark
Art of Noise
Laurie Anderson
Tom Waits
Elvis Costello
Phish
Fatboy Slim
Not everyone’s cup of tea musically, but very cool.
For me, as far as “cool”, I always felt that Violator-era Depeche Mode was the epitome. The band shots in the Enjoy the Silence video are awesome.
Well, I meant the entire ensemble (since you asked about bands), not just Baker. You saying Gerry is NOT cool?
Incidentally, I wouldn’t comsider Mingus cool, either. Mingus is HOT. At the risk of offending Eve, I would say that Trumbauer’s band is hot, too.
“Hot” in the archaic jazz sense, meaning burning with emotion and fervor. Musicians loaded on benzedrine, reefer, and/or bootleg hooch. The Mulligan/Baker quartet was COOL. Intellectual, complex, studied, heroin-fueled.
How’s about Pink Floyd
I can’t believe I forgot to mention how cool Depeche Mode was. I’ve been a fan since I was six, fer cryin’ out loud. I was around that age when Violator came out. I must now pray to my shrine to David Gahan and flay the skin from by back with an enraged cat.
You’re so sexy when you’re pissed off. Your whole face just lights up.
So, the Fonz was never cool?
James Dean was never cool?
OH PLEASE.
As for the Tont Bennett comment, that’s quite possibly the stupidest and least informed comment I’ve heard about ANYTHING in the last two years.
You obviously haven’t been to a Tony Bennett concert, not just in the past 8 years, but in your life.
Also, your comment about forty-five year old women and crusty D-cups and granny panties is beyond asinine to say the least. I doubt that either Susan Sarandon OR Michelle Pheiffer wear granny panties.
Why thank you. 
I guess other peoples’ ignorance brings out the best in me.
I’m with TheBip, Aerosmith it is.
“Love in an elevatoer / Livin’ it up when I’m going down”
Who else could pull that off?
At his peak, abolsutely no rock musician who has ever lived has ever been as cool as Elvis was. I’m not even an Elvis fan, but folks, NOBODY was as cool as Elvis. I’m appalled anyone would forget that.
He was the absolute epitome of cool; really, really good at what he was doing but at the same time irreverent about it. That’s what cool IS. “Cool” is “irreverent competence.”
Everyone is making the mistake of thinking “cool” means “really great music.” A cool band or artist must make at least decent music, but you can make great music and be decidedly uncool. REM makes great music but aren’t the least bit cool; they have always come off as shrill and faddish, and you cannot be cool while being shrill. Peter Gabriel has made some wonderful music but he’s pompous, and you absolutely cannot be pompous and be cool. The Doors were almost cool, but took themselves far too seriously, inasmuch as Jimbo could take himself seriously through his booze-addled brain. You cannot take yourself very seriously and be cool. Rush - way, way too serious about themselves. Midnight Oil? Forget it; they made great music but wouldn’t know cool if it hit them in the face. Pearl Jam is so uncool they’re blistering from the lack of coolness.
Now, Elvis Costello is very cool, and I don’t even like his music. The Clash was cool. The Tragically Hip used to be incredibly cool but are very uncool now. Motorhead was cool. Nirvana was cool, although I never understood why people thought their music was very good. Aerosmith was cool, but are over the hill now. Velvet Underground was cool. CCR was cool. Aretha was so cool she was freezing. The Chili Peppers, tres cool. Ray Charles, Wilson Pickett, and Al Green were very cool, but James Brown was not as cool as he has been given credit for being.
Some great suggestions so far, I’m just going to add one so far missing…
How about Robert Johnson? King of Delta blues, sold his soul to the Devil (legendarily) and was killed over another man’s woman in a bar.
Most of the bands and music I like are sorta Anti-Cool, they’re not popular… don’t really care to be and would never be anybody’s current idea of what’s ‘cool’. I recall a Simpson’s quote along those lines…
Umm, okay, WSLer, maybe I completely missed the point of Happy Days, but I really never thought The Fonz was supposed to be cool. He seemed to me to be a parody of what coolness was supposed to be. Of course, I never saw the show until the late eighties, so maybe I missed the context of the times.
See, there’s a huge difference between James Dean and Tony Bennett. James Dean, while a teen idol, died before he could become uncool. Dying young is practically a sure-fire ticket to perpetual coolness. Oh, and Susan Sarandon wears granny panties. You can see 'em in The Rocky Horror Picture Show
Anyway, while I have no idea how old you are, this is really starting to remind me of a conversation across the generation gap, so I’m gonna stop participating. We’ll just have to say that you have your cool, and I have mine.
Bands that do not produce really good music are not cool.
Bands that do are cool by definition.
The purpose of a band is music! That’s the whole point!
So, the Beatles were cool.
Let’s face it-- the appearance of a band is dictated by agents, promoters & fat cats. It’s an empty standard to like a band based on a phoney & synthetic image. :rolleyes:
Ask the musicians–the cool comes from the sound. 
IMHO, Disaster Area
The concerts took place on a deserted planet, and the sound
was mixed from a concrete bunker, 37 miles from the stage.
Now that’s cool.